N-[(2S,3R,4R,5S,6R)-2-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide | 183051-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5S,6R)-2-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide
• CAS: 183051-88-9
• 化学式: C₃₇H₄₇NO₁₁
• 分子量: 681.78
• InChiKey: HKYPVOPNPAIRRR-LZQVQZKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  49.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  154.4
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5S,6R)-2-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide 在 盐酸 、 calcium sulfate 、 4 A molecular sieve 、 左旋樟脑磺酸 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 乙醚 为溶剂， 反应 22.17h， 生成
  参考文献：
  名称：

  A highly practical synthesis of the sialyl Lewis X pentasaccharide and an investigation of binding to E-, P-, and L-Selectins

  摘要：

  A practical synthesis of the sialyl Lewis X (sLe(x)) pentasaccharide, NeuAc alpha 2-3Gal beta 1-4(Fuc alpha 1-3)GlcNAc alpha 1-3Gal beta OEt (1), as a potential blocker for E-selectin has been described. The glycosylation of a trisaccharide acceptor, Fuc alpha(1-3)GlcNAc beta(1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha(2-3)Gal beta SMe, did not yield the desired sLe(x) pentasaccharide 1 at all. However, the glycosylation of a disaccharide acceptor, GlcNAc beta(1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha(2-3)Gal beta SMe, quantitatively yielded the tetrasaccharide NeuAc alpha(2-3)Gal beta(1-4)GlcNAc beta(1-3)Gal beta OEt. This tetrasaccharide is readily converted to the title compound in a high yield by fucosylation, followed by deprotection. The inhibitory activities of compound 1 toward the binding of the natural ligand (sLe(x)) with the E-, P-, and L-selectins were stronger than those of the sLe(x) tetrasaccharide. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00105-8
• 作为产物：
  描述：

  ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside 在 甲醇 、 4 A molecular sieve 、 sodium methylate 、 silver perchlorate 、 一水合肼 、 silver carbonate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 44.17h， 生成 N-[(2S,3R,4R,5S,6R)-2-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  A highly practical synthesis of the sialyl Lewis X pentasaccharide and an investigation of binding to E-, P-, and L-Selectins

  摘要：

  A practical synthesis of the sialyl Lewis X (sLe(x)) pentasaccharide, NeuAc alpha 2-3Gal beta 1-4(Fuc alpha 1-3)GlcNAc alpha 1-3Gal beta OEt (1), as a potential blocker for E-selectin has been described. The glycosylation of a trisaccharide acceptor, Fuc alpha(1-3)GlcNAc beta(1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha(2-3)Gal beta SMe, did not yield the desired sLe(x) pentasaccharide 1 at all. However, the glycosylation of a disaccharide acceptor, GlcNAc beta(1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha(2-3)Gal beta SMe, quantitatively yielded the tetrasaccharide NeuAc alpha(2-3)Gal beta(1-4)GlcNAc beta(1-3)Gal beta OEt. This tetrasaccharide is readily converted to the title compound in a high yield by fucosylation, followed by deprotection. The inhibitory activities of compound 1 toward the binding of the natural ligand (sLe(x)) with the E-, P-, and L-selectins were stronger than those of the sLe(x) tetrasaccharide. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00105-8